US9790313B2 - Curing compositions and methods of preparing - Google Patents

Curing compositions and methods of preparing Download PDF

Info

Publication number
US9790313B2
US9790313B2 US14/831,586 US201514831586A US9790313B2 US 9790313 B2 US9790313 B2 US 9790313B2 US 201514831586 A US201514831586 A US 201514831586A US 9790313 B2 US9790313 B2 US 9790313B2
Authority
US
United States
Prior art keywords
melamine
curing composition
curing
resin systems
reaction mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
US14/831,586
Other languages
English (en)
Other versions
US20160053043A1 (en
Inventor
Ganapathy S. Viswanathan
Craig M. ZIRKLE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bakelite UK Holding Ltd
Original Assignee
Hexion Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hexion Inc filed Critical Hexion Inc
Priority to US14/831,586 priority Critical patent/US9790313B2/en
Assigned to HEXION INC. reassignment HEXION INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VISWANATHAN, GANAPATHY S., ZIRKLE, CRAIG M.
Assigned to WILMINGTON TRUST, NATIONAL ASSOCIATION reassignment WILMINGTON TRUST, NATIONAL ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION INC.
Assigned to WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT reassignment WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION INC.
Assigned to WILMINGTON TRUST, NATIONAL ASSOCIATION reassignment WILMINGTON TRUST, NATIONAL ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION INC.
Publication of US20160053043A1 publication Critical patent/US20160053043A1/en
Assigned to WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT reassignment WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION INC.
Assigned to HEXION INC. reassignment HEXION INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: WILMINGTON TRUST, NATIONAL ASSOCIATION
Publication of US9790313B2 publication Critical patent/US9790313B2/en
Application granted granted Critical
Assigned to WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT reassignment WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Assignors: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
Assigned to JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT reassignment JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT PATENT SECURITY INTEREST (ABL) Assignors: HEXION INC.
Assigned to JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT reassignment JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT PATENT SECURITY INTEREST (TERM LOAN) Assignors: HEXION INC.
Assigned to GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT reassignment GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION VAD LLC
Assigned to HEXION INC. reassignment HEXION INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: JPMORGAN CHASE BANK, N.A.
Assigned to HEXION INC. reassignment HEXION INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: JPMORGAN CHASE BANK, N.A.
Assigned to HEXION VAD LLC reassignment HEXION VAD LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEXION INC.
Assigned to BAKELITE LLC reassignment BAKELITE LLC CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: HEXION VAD LLC
Assigned to Bakelite UK Holding Ltd. reassignment Bakelite UK Holding Ltd. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAKELITE LLC
Assigned to GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT reassignment GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Bakelite UK Holding Ltd., ENERG2 TECHNOLOGIES, INC., GEORGIA-PACIFIC CHEMICALS LLC, GEORGIA-PACIFIC CONSUMER PRODUCTS LP, KOCH AGRONOMIC SERVICES LLC, Surface Tech LLC
Assigned to MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT reassignment MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Bakelite UK Holding Ltd., ENERG2 TECHNOLOGIES, INC., GEORGIA-PACIFIC CHEMICALS LLC, GEORGIA-PACIFIC CONSUMER PRODUCTS LP, KOCH AGRONOMIC SERVICES LLC
Assigned to HEXION VAD LLC reassignment HEXION VAD LLC RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
    • C08G12/12—Ureas; Thioureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the invention relates to curing compositions for resin systems and in particular for phenolic resin systems and epoxy resin systems, to methods of preparing the curing compositions and to resin systems incorporating same.
  • the curing compositions of the invention are the reaction product of an aldehyde with an amine in the presence of an aprotic solvent.
  • FIG. 1 is a plot of heat flow as a function of temperature illustrating the curing behavior of the intermediate obtained in Example 1.
  • FIG. 2 is a plot of heat flow as a function of temperature illustrating the curing behavior of the intermediate obtained in Example 5.
  • the invention is a curing composition for phenolic resin systems or epoxy resin systems, which curing composition is a reaction product of an aldehyde and an amine which may be an aminotriazine containing at least one free amino group, urea, a derivative of urea containing at least one free amino group, and any combinations or subset thereof.
  • the invention is a curing composition for thermoset phenolic resin systems or thermoset epoxy resin systems, which curing composition is a reaction product of an aldehyde and an amine which may be an aminotriazine containing at least one free amino group, urea, a derivative of urea containing at least one free amino group, and any combinations or subset thereof.
  • the invention is a curing composition for a resin system which is the reaction product of an aldehyde and an amine selected from one or more of an aminotriazine containing at least one free amino group, urea, or a derivative of urea containing at least one free amino group, where the reaction occurs in the presence of an aprotic solvent.
  • the amine includes one or more aminotriazines containing at least one free amino group.
  • the amine includes one or more of a 1,3,5-triazine, melamine, a substituted melamine, a guanamine or a derivative of guanaimine.
  • the amine includes urea, or a derivative of urea containing at least one free amino group.
  • the amine is melamine or urea or a combination thereof.
  • the invention is a method for isolating the curing composition intermediate which includes the step of adding an organic solvent to the reaction product, which organic solvent may or may not be an aprotic solvent, to precipitate the intermediate out of solution.
  • the method further includes the step of adding water to re-solubilized the intermediate.
  • the curing composition of the invention is the reaction product of an aldehyde with an amine in the presence of an aprotic solvent.
  • the aldehyde may be an aldehyde added directly or formed in situ.
  • aldehyde of the formula R—CHO may be used, wherein R is a aliphatic, cycloaliphatic or aromatic moiety.
  • R is a aliphatic, cycloaliphatic or aromatic moiety containing about 1-8 carbon atoms such as acetaldehyde, propionaldehyde, benzaldehyde, furfuraldehyde, paraformaldehyde, the solid low molecular weight polymer of formaldehyde, and the like.
  • the aldehyde is formaldehyde in the solid or aqueous form (formalin).
  • formaldehyde may be used or formed in situ.
  • paraformaldehyde, polyoxymethylene, hexamethylenetetramine, or trioxane may be used as a compound to form formaldehyde in situ.
  • the aldehyde may be a di-functional aldehyde such as for example glyoxal.
  • the curing composition is free of added formaldehyde.
  • the amine is an aminotriazine containing at least one free amino group.
  • the amine is an aminotriazine such as, for example, a 1,3,5-triazine, melamine or a substituted melamine (e.g., an alkylmelamine such as 2-methylmelamine, guanylmelamine), a guanamine or a derivative thereof (e.g., guanamine, methylguanamine, acetoguanamine, benzoguanamine, succinoguanamine and CTU-guanamine).
  • a substituted melamine e.g., an alkylmelamine such as 2-methylmelamine, guanylmelamine
  • a guanamine or a derivative thereof e.g., guanamine, methylguanamine, acetoguanamine, benzoguanamine, succinoguanamine and CTU-guanamine.
  • the amine is selected from urea, or a derivative of urea containing at least one free amino group.
  • the amine compound is melamine or urea or a combination thereof.
  • the amine compound is not an aniline. In one embodiment the reaction is free of a catalyst.
  • the solvent may be any aprotic solvent known in the art as not capable of hydrogen bonding, such as, for example perfluorohexane, ⁇ , ⁇ , ⁇ -trifluorotoluene, pentane, hexane, cyclohexane, methylcyclohexane, decalin, dioxane, carbon tetrachloride, freon-11, benzene, toluene, triethyl amine, carbon disulfide, diisopropyl ether, diethyl ether, t-butyl methyl, chloroform, ethyl acetate, 1,2-dimethoxyethane, 2-methoxyethyl ether, tetrahydrofuran, methylene chloride, pyridine, 2-butanone, acetone, hexamethylphosphoramide, N-methylpyrrolidinone (NMP), nitromethane, dimethylformamide, acet
  • the amine and aldehyde reactants are contacted at a temperature of between about 30° C. and about 80° C. In another embodiment the reactants are contacted for about 30 minutes to 30 hours, or about 30 minutes to about 24 hours or about 30 minutes to about 12 hours or about 30 minutes to about 5 hours. In another embodiment, the reactants are contacted, in an amount such that for every 2 amino groups there are 2.5 to 5 equivalents of aldehyde. In another embodiment, the reactants are contacted in a mole ratio of amine to aldehyde of about 1:3 to about 1:8 or about 1:3 to about 1:6, or about 1:3 to about 1:5, or about 1:4.
  • the resultant product is expected to be an intermediate, which can be used as a binder or as a co-curative for epoxy and phenolic resins.
  • the intermediate may be subjected to heating to form a hexahydrotriazine system.
  • the intermediate may be subjected to a temperature to initiate a curing mechanism.
  • the temperature to initiate a curing mechanism is greater than 100° C.
  • the intermediate may undergo polycylcotrimerization with or without the use of a catalyst.
  • the intermediate is water soluble.
  • the curing agent of the invention is prepared in accordance to the following generic reaction scheme:
  • the curing compositions of the invention may be included in resin systems used in a wide variety of applications.
  • the curing compositions of the invention may be included in resin systems used in the manufacture of structural composites, for example, in the automotive, marine and aerospace industries.
  • the curing compositions of the invention may be included in resin systems used in the manufacture of electrical laminates, such as used in printed circuit boards.
  • the curing compositions of the invention may be included in resin systems used in the manufacture of coating compositions.
  • the curing compositions of the invention may be included in resin systems used in the manufacture of friction materials.
  • the product was completely soluble in the reaction mixture. Upon addition of an organic solvent (acetone, acetyl nitrile, methanol, ethanol, isopropanol) or water the product stays in solution.
  • an organic solvent acetone, acetyl nitrile, methanol, ethanol, isopropanol
  • NMP N-methyl-2-pyrrolidone
  • benzoguanamine 0.267 moles
  • reaction mixture never solubilized.
  • organic solvent acetone, acetyl nitrile, methanol, ethanol, isopropanol
  • water the material never dissolved or increased in precipitate.
  • NMP N-methyl-2-pyrrolidone
  • 30 g 50% aqueous formalin 0.99 moles
  • the reaction mixture was heated to 75° C. and 15 g melamine (0.119 moles) was added at once.
  • the reaction mixture was held at 75° C. for 20 minutes at which time the solution formed a soft gel.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
US14/831,586 2014-08-21 2015-08-20 Curing compositions and methods of preparing Active US9790313B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/831,586 US9790313B2 (en) 2014-08-21 2015-08-20 Curing compositions and methods of preparing

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462040362P 2014-08-21 2014-08-21
US14/831,586 US9790313B2 (en) 2014-08-21 2015-08-20 Curing compositions and methods of preparing

Publications (2)

Publication Number Publication Date
US20160053043A1 US20160053043A1 (en) 2016-02-25
US9790313B2 true US9790313B2 (en) 2017-10-17

Family

ID=55347737

Family Applications (1)

Application Number Title Priority Date Filing Date
US14/831,586 Active US9790313B2 (en) 2014-08-21 2015-08-20 Curing compositions and methods of preparing

Country Status (2)

Country Link
US (1) US9790313B2 (fr)
WO (1) WO2016029038A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2696859C1 (ru) * 2018-10-15 2019-08-07 Игорь Вячеславович Парунов Аминопластичная смола

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB795504A (en) 1955-10-03 1958-05-21 Armour & Co Improved triazine compounds and strip-resistant bituminous compounds containing the same
US3026285A (en) 1959-09-18 1962-03-20 Frank N Hirosawa Curing agent comprising the reaction product of an aliphatic polyamine and an aldehyde, and epoxy resin cured therewith
US3131086A (en) 1962-01-04 1964-04-28 American Cyanamid Co Thermosetting amino-phenoplast resins
US3468830A (en) 1966-08-26 1969-09-23 Pall Corp Curing of epoxide resins with the reaction product of an organic amine and an aldehyde,and curing and resin compositions and process
US3488310A (en) * 1967-02-24 1970-01-06 Owens Corning Fiberglass Corp Urea-melamine-formaldehyde resins
US3840495A (en) 1970-10-23 1974-10-08 Rhone Poulenc Sa Heat-stable polymers based on bis-imides and oligomeric amines
US4088620A (en) * 1972-12-28 1978-05-09 Kuraray Co., Ltd. Melamine resin flame-retardant fibers
US4138445A (en) * 1974-05-21 1979-02-06 Toray Industries, Inc. Flame retardant fiber
JPS63192759A (ja) 1987-02-06 1988-08-10 Mitsubishi Gas Chem Co Inc ヘキサヒドロ−ｓｙｍ−トリアジン構造を有するポリ三級アミン化合物の製造方法
US5162049A (en) 1991-09-09 1992-11-10 Ethyl Petroleum Additives Middle distillate fuels and additives therefor
US5215547A (en) 1991-09-09 1993-06-01 Ethyl Petroleum Additives, Inc. Middle distillate fuels and additives therefor
WO1997025126A2 (fr) 1996-01-10 1997-07-17 Quaker Chemical Corporation Procede et composition de regeneration destines a enlever des sulfures de courants gazeux
US5665851A (en) 1994-08-22 1997-09-09 Sequa Chemicals, Inc. Aminoplastic resins and their use as a crosslinking agent for cellulose
US5998573A (en) * 1995-09-18 1999-12-07 Nissan Chemical Industries, Ltd. Amino resin composition
WO2001098388A1 (fr) 2000-06-23 2001-12-27 Basf Aktiengesellschaft Reseaux polymeres aldehyde / polyetheramine
JP2004043547A (ja) 2002-07-09 2004-02-12 Nippon Steel Chem Co Ltd イミド構造を有する熱硬化性樹脂、その硬化物及び熱硬化性樹脂組成物
CN101265255A (zh) 2008-04-28 2008-09-17 四川大学 含三嗪结构的苯并噁嗪中间体的制备方法
US20090247709A1 (en) 2008-03-27 2009-10-01 Case Western Reserve University Diamine polymer and resin composition thereof
US20120238653A1 (en) 2009-10-09 2012-09-20 Henkel Ag & Co. Kgaa Latent curing agent and epoxy compositions containing the same
CN102827095A (zh) 2012-09-07 2012-12-19 成都金桨高新材料有限公司 一种含芳酰胺的苯并噁嗪树脂中间体及其制备方法
US20130217824A1 (en) 2010-09-30 2013-08-22 Ram Gupta Non-etherified reaction product of a cyclic urea and a multifunctional aldehyde
US9522358B2 (en) * 2010-09-24 2016-12-20 Agency For Science, Technology And Research Porous polymer material

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB795504A (en) 1955-10-03 1958-05-21 Armour & Co Improved triazine compounds and strip-resistant bituminous compounds containing the same
US3026285A (en) 1959-09-18 1962-03-20 Frank N Hirosawa Curing agent comprising the reaction product of an aliphatic polyamine and an aldehyde, and epoxy resin cured therewith
US3131086A (en) 1962-01-04 1964-04-28 American Cyanamid Co Thermosetting amino-phenoplast resins
US3468830A (en) 1966-08-26 1969-09-23 Pall Corp Curing of epoxide resins with the reaction product of an organic amine and an aldehyde,and curing and resin compositions and process
US3488310A (en) * 1967-02-24 1970-01-06 Owens Corning Fiberglass Corp Urea-melamine-formaldehyde resins
US3840495A (en) 1970-10-23 1974-10-08 Rhone Poulenc Sa Heat-stable polymers based on bis-imides and oligomeric amines
US4088620A (en) * 1972-12-28 1978-05-09 Kuraray Co., Ltd. Melamine resin flame-retardant fibers
US4138445A (en) * 1974-05-21 1979-02-06 Toray Industries, Inc. Flame retardant fiber
JPS63192759A (ja) 1987-02-06 1988-08-10 Mitsubishi Gas Chem Co Inc ヘキサヒドロ−ｓｙｍ−トリアジン構造を有するポリ三級アミン化合物の製造方法
US5215547A (en) 1991-09-09 1993-06-01 Ethyl Petroleum Additives, Inc. Middle distillate fuels and additives therefor
US5162049A (en) 1991-09-09 1992-11-10 Ethyl Petroleum Additives Middle distillate fuels and additives therefor
US5665851A (en) 1994-08-22 1997-09-09 Sequa Chemicals, Inc. Aminoplastic resins and their use as a crosslinking agent for cellulose
US5998573A (en) * 1995-09-18 1999-12-07 Nissan Chemical Industries, Ltd. Amino resin composition
WO1997025126A2 (fr) 1996-01-10 1997-07-17 Quaker Chemical Corporation Procede et composition de regeneration destines a enlever des sulfures de courants gazeux
WO2001098388A1 (fr) 2000-06-23 2001-12-27 Basf Aktiengesellschaft Reseaux polymeres aldehyde / polyetheramine
JP2004043547A (ja) 2002-07-09 2004-02-12 Nippon Steel Chem Co Ltd イミド構造を有する熱硬化性樹脂、その硬化物及び熱硬化性樹脂組成物
US20090247709A1 (en) 2008-03-27 2009-10-01 Case Western Reserve University Diamine polymer and resin composition thereof
CN101265255A (zh) 2008-04-28 2008-09-17 四川大学 含三嗪结构的苯并噁嗪中间体的制备方法
US20120238653A1 (en) 2009-10-09 2012-09-20 Henkel Ag & Co. Kgaa Latent curing agent and epoxy compositions containing the same
US9522358B2 (en) * 2010-09-24 2016-12-20 Agency For Science, Technology And Research Porous polymer material
US20130217824A1 (en) 2010-09-30 2013-08-22 Ram Gupta Non-etherified reaction product of a cyclic urea and a multifunctional aldehyde
CN102827095A (zh) 2012-09-07 2012-12-19 成都金桨高新材料有限公司 一种含芳酰胺的苯并噁嗪树脂中间体及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Thermosets Built to Break Down," Eco Report, VIA C&EN Chemical & Engineering News, May 19, 2014.

Also Published As

Publication number Publication date
US20160053043A1 (en) 2016-02-25
WO2016029038A1 (fr) 2016-02-25

Similar Documents

Publication Publication Date Title
JP6046716B2 (ja) ベンゾオキサジン化合物の生産方法
US8911858B2 (en) Multifunctional melamine epoxy resins, methylols and amines
JP5775306B2 (ja) 改質フェノール樹脂
US9790313B2 (en) Curing compositions and methods of preparing
US8802848B2 (en) Melamine based mannich-compounds and a process for obtaining the same
RU2447057C2 (ru) Гидрокси-ароматическое соединение, способ его получения и применение соединения
US20190010416A1 (en) Liquid phenolic resol resin, method for preparing liquid phenolic resol resin, and article
US20090326164A1 (en) Process for the preparation of a hydroxy-aromatic resin: hydroxy-aromatic resin, and modification thereof
KR20090024135A (ko) 하이드록시-방향족 수지의 제조 방법, 하이드록시-방향족 수지 및 그의 개질 방법
KR102013976B1 (ko) 개질된 아미노 수지
KR101828110B1 (ko) 시클릭 우레아와 다관능성 알데히드의 비에테르화 반응 생성물
CA2202643C (fr) Derives acetal de composes de resol
US20150065756A1 (en) Liquid resol-type phenolic resin and wet paper friction material
RU2425064C1 (ru) 3-фенил-3-[4 &#39;-гидрокси-3 &#39;, 5 &#39;-ди(гидроксиметил)-фенил]фталид в качестве мономера для получения фенолформальдегидных фталидсодержащих олигомеров и в качестве отвердителя для получения сшитых фталидсодержащих полимеров, способ его получения, композиция на его основе для получения фталидсодержащих сшитых полимеров и фталидсодержащий полимер
JP7035516B2 (ja) フェノール類変性キシレン樹脂及びその製造方法
US2631991A (en) Pyrazoline resins
JP3207412B2 (ja) 粉末フェノール系樹脂の製造方法
JP3207411B2 (ja) フェノール系共縮合樹脂の製造方法
Kim Renewable polyol‐based polycarbamates and polycarbamate–formaldehyde thermosetting resins
US2710850A (en) Cyanoacetic acid ester resins
JP2005336227A (ja) 固形レゾール型フェノール樹脂の製造方法
PL417458A1 (pl) Sposób otrzymywania mieszaniny hydroksymetylowych pochodnych melemu oraz sposób zastosowania tej mieszaniny
US20190135985A1 (en) Polyoxymethylene and Siloxane Block Copolymers and Process For Making Same
CN104744695A (zh) 一种硫酸酯撑型苯并噁嗪树脂的制备方法

Legal Events

Date Code Title Description
AS Assignment

Owner name: HEXION INC., OHIO

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:VISWANATHAN, GANAPATHY S.;ZIRKLE, CRAIG M.;REEL/FRAME:036390/0686

Effective date: 20150820

AS Assignment

Owner name: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT, DEL

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:036822/0804

Effective date: 20150930

Owner name: WILMINGTON TRUST, NATIONAL ASSOCIATION, MINNESOTA

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:036822/0625

Effective date: 20150930

AS Assignment

Owner name: WILMINGTON TRUST, NATIONAL ASSOCIATION, MINNESOTA

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:037639/0795

Effective date: 20151231

AS Assignment

Owner name: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT, MINNESOTA

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:041693/0888

Effective date: 20170208

Owner name: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATE

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:041693/0888

Effective date: 20170208

AS Assignment

Owner name: HEXION INC., OHIO

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:WILMINGTON TRUST, NATIONAL ASSOCIATION;REEL/FRAME:041794/0038

Effective date: 20170208

STCF Information on status: patent grant

Free format text: PATENTED CASE

AS Assignment

Owner name: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRE

Free format text: PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT;ASSIGNOR:WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT;REEL/FRAME:048788/0617

Effective date: 20190329

Owner name: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT, DELAWARE

Free format text: PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT;ASSIGNOR:WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT;REEL/FRAME:048788/0617

Effective date: 20190329

AS Assignment

Owner name: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT, IL

Free format text: PATENT SECURITY INTEREST (ABL);ASSIGNOR:HEXION INC.;REEL/FRAME:049740/0770

Effective date: 20190701

Owner name: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT, IL

Free format text: PATENT SECURITY INTEREST (TERM LOAN);ASSIGNOR:HEXION INC.;REEL/FRAME:049741/0425

Effective date: 20190701

Owner name: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT, ILLINOIS

Free format text: PATENT SECURITY INTEREST (TERM LOAN);ASSIGNOR:HEXION INC.;REEL/FRAME:049741/0425

Effective date: 20190701

Owner name: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT, ILLINOIS

Free format text: PATENT SECURITY INTEREST (ABL);ASSIGNOR:HEXION INC.;REEL/FRAME:049740/0770

Effective date: 20190701

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4

AS Assignment

Owner name: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT, TEXAS

Free format text: SECURITY INTEREST;ASSIGNOR:HEXION VAD LLC;REEL/FRAME:056145/0957

Effective date: 20210430

AS Assignment

Owner name: HEXION INC., OHIO

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A.;REEL/FRAME:056219/0677

Effective date: 20210430

Owner name: HEXION INC., OHIO

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:JPMORGAN CHASE BANK, N.A.;REEL/FRAME:056219/0582

Effective date: 20210430

AS Assignment

Owner name: HEXION VAD LLC, KENTUCKY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HEXION INC.;REEL/FRAME:057323/0086

Effective date: 20210430

AS Assignment

Owner name: BAKELITE UK HOLDING LTD., UNITED KINGDOM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BAKELITE LLC;REEL/FRAME:060377/0699

Effective date: 20211025

Owner name: BAKELITE LLC, KENTUCKY

Free format text: CHANGE OF NAME;ASSIGNOR:HEXION VAD LLC;REEL/FRAME:059926/0973

Effective date: 20211022

AS Assignment

Owner name: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT, KENTUCKY

Free format text: SECURITY INTEREST;ASSIGNORS:GEORGIA-PACIFIC CHEMICALS LLC;GEORGIA-PACIFIC CONSUMER PRODUCTS LP;ENERG2 TECHNOLOGIES, INC.;AND OTHERS;REEL/FRAME:060328/0327

Effective date: 20220608

Owner name: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT, NEW YORK

Free format text: SECURITY INTEREST;ASSIGNORS:GEORGIA-PACIFIC CHEMICALS LLC;GEORGIA-PACIFIC CONSUMER PRODUCTS LP;ENERG2 TECHNOLOGIES, INC.;AND OTHERS;REEL/FRAME:060328/0250

Effective date: 20220608

AS Assignment

Owner name: HEXION VAD LLC, KENTUCKY

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.;REEL/FRAME:060209/0558

Effective date: 20220527